Molly Jenson has been a professional touring singer for almost 20 years. She’s written songs and sung with artists like Sean and Sara Watkins of Nickel Creek, Schuyler Fisk, Greg Laswell, and Jon Foreman of Switchfoot.

I first saw Molly perform at a decades-old beloved coffee house in San Diego called Lestat’s, a place one of the singer-songwriters called, “a safe place to fail.”

Molly sang one of her most popular songs, “Give It Time,”  at the end, and the moment I heard it I knew I’d want to profile her. Some of my favorite lyrics:

Where are you off to

in such a hurry, girl?

Is something chasing you?

What has you spinning round

in circles, little girl?

is it the world or

is it you?

There’s no use trying to stop this

There’s no use trying to make it go away

Before you disappear

Just give it time

What are you hiding from?

What do you think will happen?

If you see this one through?

Molly and I meet a few weeks later at my favorite coffee shop in San Diego. She’s tall, with cropped white-blonde hair and sharp bangs, wearing thrifted overalls. She’s gorgeous and cool and her fashion and tattoos have that thing that all musicians I’ve ever met have—a kind of chaos perfection. Their style seems to represent them so fully, as if to say growing up and being boring is and always has been optional.

Molly orders avocado toast and we start talking about how she became an artist.

Molly was in every choir, play, and musical growing up. She performed every chance she could get. In college, she toured with a band.

And in many ways that began the cycle of what would become her life.

Go on tour. Go back home to San Diego. Work at a coffee shop to pay rent. Repeat.

When one coffee shop stint became longer than expected, she got restless. Her mom mentioned that one of their family friends, Adam Gillespie, was working for a local band and helping them with their merch. The band was growing in popularity. Molly asked Adam if he needed any help.

He said no, he was good, but thanks.

Molly kept working at the coffee shop.

Two weeks later, Adam called and said, “You know what, I actually do need help.”

That’s how Molly began working for the band Switchfoot.

Adam hired her on a trial basis. She’d never worked in merch before and didn’t know Photoshop, but she took the opportunity, learned quickly, and proved herself to be invaluable.

Molly worked with Switchfoot full-time for five years, and for many more after that in between other tours.

Molly was also starting to taken an interest in songwriting when a friend from college, Greg Laswell, became a producer. He asked her if she wanted to make an album. She wasn’t sure if she could do it, but they met up and finished her first song in a day. The songs kept coming. They recorded all of them.

Molly says now how crazy it was to record the first songs she ever wrote. She’s been in the business long enough now to know that most professional recording artists start with about 50 songs and then choose the final 10 for the album.

But there was a boldness in her first album. She just did it.

Something magical happened at the end.

“I didn’t write any of the songs for the album by myself,” Molly explains. “I wrote them all with Greg. But then the guy I was dating broke up with me and suddenly I wrote the last song for the album in 30 minutes. It was the first thing I’d ever written completely by myself and I was just like ‘Oh my gosh I can do this. I’ve learned how to write songs.’”

That album gave her the ability to do something she’d never done before—sing her own songs, instead of someone else’s. She began performing her songs in front of people, starting with Lestat’s coffee house. And then Molly decided to move to Nashville and play house concerts for a living. I had no idea then what a house concert was. I had questions:

“So, you, like, play in people’s houses?” I ask.

“Yep! It’s a house.”

“Like, someone’s personal house?”

“Yep! I’d go in the living room and I would play in their house. If it was a small crowd I wouldn’t plug in. Those were the best because I felt so connected. I’m still friends with a lot of the people I played house concerts for.”

“So is it like a party? Do people hire musicians to come to their home for parties or do they just decide to host a concert in their house?”

“Yep, both!”

“How did you find the people who would hire you to play in their home?”

“I had an email list. I would just send out an email and say ‘Hey I’m looking for a place to do some house concerts, let me know if you’re interested and I’ll send you information.’”

Molly built her email list by having a sign up form at all of her shows, and on her website.

Molly made a full-time living doing house concerts for a year. No booking agent. No manager. Just a girl and her guitar and her email list.

The songs she played were mostly sad and serious, but in between songs, she’d joke and make people laugh.

At Lestat’s, all the musician’s that performed that night sang a Beatles song together. When it was Molly’s turn for a mini solo, she kept the melody to “All You Need is is Love” but instead sang “Oops I forgot the words to this paaaaart, this is what you get when you don’t memoriiiiiiize it.” The lyrics were wrong but the melody (and her voice) were perfect.

And she made everyone laugh.

“The truth is,” Molly says, “I feel more connected to an audience when I get a laugh. Awkward moments are my dream come true. When I get a laugh all my fears and insecurities just go away and I feel connected.”

Once, after a show, a man walked up to give her some unsolicited advice. “Your songs are pretty good,” he said, “but you’re too manic. Your songs are really sad and then you’re funny in between and it’s confusing to people.”

This hurt her at the time. Now, in her late 30’s, she sees it differently. “Now I realize that what some people don’t like is usually the stuff you should keep doing,” she says. “Because it’s different, it’s the stuff nobody else is doing.”

Molly kept singing, touring, and making people laugh. She moved around the country, worked with a variety of bands, and even got married and started a videography business with her husband.

Then she was faced with an unexpected divorce sent her life into a reboot, both personally and creatively, and it was painful. Molly turns 40 next year, and, for the moment, when she’s not touring, she’s living with her parents.

“I never thought I would be divorced,” she says, “or that I’d be single at this age or not have kids. But I can either wallow and feel really sorry for myself (which I have done plenty) or I can get up every day and do the next thing I need to do for my life. I’m not going to be living at my parents’ house forever.”

She started writing in the fissure: lyrics, poetry, cartoons, sketch comedy, standup.

“I was listening to this podcast interview yesterday,” Molly says, “and the woman being interviewed talked about how she reinvented herself at 45. I realized it doesn’t matter how old I am. So I’m just trying to figure it all out right now and take care of myself: meditate, exercise, go the movies, organize my life, and go on auditions.”

To make money, she’s doing voiceover work, which involves a lot of auditions and a lot of rejection.

“I learned from Jenna Fischer’s book that after you do an audition you just have to walk away and forget about it,” Molly says. “I have to remind myself that auditions are the job. If you do 50 auditions and get one job out of that, that’s awesome. I have to keep reminding myself that auditions are just practice and the more no’s I get the closer I get to a yes.”

But sometimes, a yes turns into a no, and it’s hard to come back from.

For Molly, that happened after a friend asked her to help produce a tribute to Emmylou Harris in New York. One of the artists a part of the tribute was actress and country star Jennifer Nettles of Sugarland. Molly was asked to sing harmonies with Jennifer. Afterward, Jennifer asked Molly if she was free to come on tour with Sugarland as a backup singer.

Molly was gobsmacked. “At this point I had very recently been divorced, quit my job and I’d just been house-sitting for people,” Molly says. “I didn’t have a car and had zero plans.”

Molly eventually got an email with the job offer. The manager also asked if she could sing at an event happening the following week, before the official summer tour started. But Molly was in Scotland at the time, finishing a small tour with a band she’d been with for five years. Molly told the manager she wasn’t in the country for that event, but could definitely do the summer tour.

Then, just before Valentine’s Day, Molly got an email from the Sugarland manager. They explained that the singer they’d found to fill in for for that event ended up being wonderful and they’d decided to hire her to stay on for the summer tour.

“I totally get that it was the right decision for them,” Molly says. “Jennifer even personally reached out and said ‘I’m really sorry.’ I didn’t sink to the floor when I found out, but metaphorically I did. I felt so defeated. I had started planning, and now, I had no plans. I had no idea what to do.

“I was really sad for a couple hours, and then I was like, ‘you know what, at least they know about me now.’ In the email the manager said he’d heard great things about me from Jennifer and others, and that if anything happens, I would 100% be their first call.’

“The biggest thing I’ve learned is just showing up. People aren’t going to know you’re doing stuff if you just practice in your room. I’m an introvert and I’d rather stay home most days, but I’ve learned it’s important to be getting out and finding things you can be a part of.

“After a while, people will start asking you to be a part of things. You just can’t be a recluse. And I think it’s really important to be creating. If things aren’t coming to you then make your own things.”

Two years after auditioning for a voiceover job she didn’t get, she got a call from the person who rejected her;  they remembered her and hired her for another job.

“It’s never fun to be rejected, but I’ve always had this faith that I believe things will work out the way they’re supposed to. I could be wrong, but I feel like life is too magical to give up. On my hard days I’m like ‘What am I doing?’ But on my good days I go, ‘I’m just going to do what I can do with what I have right now.’ And what I have is a journal and a laptop and basic knowledge of Photoshop. And I’m going to figure it out.”
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Learn more at mollyjenson.com.